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Old 02-15-2024, 04:58 PM   #52
jdh90
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Join Date: Nov 2015
Location: Getting Pegged
Posts: 75
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Grab 3 dildos of varying sizes and line them up small to large.

Start on your smallest dildo. Roll a die for a challenge. If you complete it, move on to the next dildo size up. If not move back one dildo. Reroll challenge each time you change dildos.

If on the first dildo and told to move back, do your failure roll.
If on the last dildo and told to move forward, do your victory roll

Challenge roll
1. Slowly sit on it until you're not holding yourself up with your legs anymore. Gently grind for 2 minutes. If you cant sit on it balls deep, go back one.
2. Insert and fully remove the dildo from your ass 100 times, then gape for 10 full seconds. If you cant gape that long, go back one.
3. Do 40 squats over the dildo, inserting and removing it each time. If your legs give out, go back one.
4. Ride it for 5 minutes, taking at least half the shaft with each thrust. If at an time you drop below 60bpm, go back one.
5. Use it to fuck your ass for 5 minutes, then squirt a hot load of fake cum inside yourself. If this dildo doesn't squirt, go back one.
6. Lay on your back and spread our legs. Fuck your ass gently for 5 minutes.

Failure roll
1. Fuck the dildos for 5 minutes each, using only spit as lube.
2. Take a 1500ml fake cum enema and plug for 1 hour.
3. Edge 10 times, then no cumming for 24 hours.
4. Sit on one of the dildos for 30 Minutes.
5. Edge 5 times, then ruin an orgasm.
6. No cumming for 7 days.

Victory roll
1. Replay but reverse the order of the dildos :P
2. Cum while you have as many dildos inside of yourself as you can fit. Stuff all your holes.
3. Edge 5 times, then cum.
4. Cum while fucking yourself with one of the dildos.
5. Buy another dildo online while riding your favorite dildo. Confirm your order as you cum.
6. Cum, lick up all fluids.
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